Nitric Acid → HCID 58563126, compound

HRID 1186143Notes

Reaction equation

HRID 1186143 reaction equation
[CH2:1]([C@@:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:9]([F:11])([F:10])[CH2:8][O:7][CH2:6][C:5]([NH2:12])=[N:4]1)[CH3:2].[N+:20]([O-])([OH:22])=[O:21].[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C@@:3]1([C:13]2[CH:18]=[C:17]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:15][C:14]=2[F:19])[C:9]([F:10])([F:11])[CH2:8][O:7][CH2:6][C:5]([NH2:12])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 58563057HCID 58563057, compound

Product 1

HCID 58563126HCID 58563126, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of (R)-5-ethyl-6,6-difluoro-5-(2-fluoro-phenyl)-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine (1.2 mmol) in sulfuric acid (5.0 ml) was added at 0° C. red fuming nitric acid (1.9 mmol) over a period of 20 min and stirring was continued for 30 min. The solution was dropped slowly into ice/water (60 ml), the pH was adjusted to 9 by addition of aqueous 4 N NaOH and extracted with ethyl acetate. The organic layer was dried, evaporated and the residue purified by chromatography on silca-NH2 using n-heptane/ethyl acetate to give (R)-5-ethyl-6,6-difluoro-5-(2-fluoro-5-nitro-phenyl)-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine as a pale yellow solid. MS: m/z=318.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. customevaporated
  4. customthe residue purified by chromatography on silca-NH2

Sources & evidence

ORD record
ord-bcd1fbf1fd2a4182964b381a2824f735
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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